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INTERVIEW: Discover Sleepy Hollow in new, mysterious ways

Photo: The Legend of Sleepy Hollow Discovery Walk features a retelling of Washington Irving’s famous tale. Photo by John Soltes.


SLEEPY HOLLOW, N.Y. — Historic Hudson Valley, the organization that preserves and grants access to a number of mansion properties in the Sleepy Hollow / Tarrytown region, knows how to throw a Halloween party. With Washington Irving’s The Legend of Sleepy Hollow as its guide, HHV is in the business of elevating this literary classic into fun fan events that allow families to enjoy some spooky good times in the locations near where the original story took place.

One can head to Irving’s Sunnyside estate for a performance of Jonathan Kruk in Irving’s Legend, a one-person retelling of the tale with puppeteers filling out the cast. They also provide Legend-inspired tours of the Sunnyside estate during the day. A few miles down the road is another one of their properties: Philipsburg Manor, located across from Sleepy Hollow Cemetery and the Old Dutch Church, which figure prominently in the original tale.

On the grounds of the manor there are numerous experiences to be enjoyed, including Spirits of Sleepy Hollow, an illusionist show, this year taking place in the theater near the gift shop. New for 2024 are two adventures that utilize the unique environment of the estate. During the day, one can enjoy the Legend of Sleepy Hollow Discovery Walk with a guide and assistant, as they re-create scenes from The Legend of Sleepy Hollow, much to the delight of attendees, many of them youngsters learning about Ichabod Crane, Brom Bones, Katrina Van Tassel and the Headless Horseman for the first time.

At night, the Philipsburg property turns into a witchy good time, thanks to the Twilight Village at Sleepy Hollow, which commandeers several areas of the estate. Patrons can have their fortunes told or purchase some holiday-themed gifts and treats. On a recent evening, a ghostly apparition on stilts mingled amongst the crowd, while fire-throwers dazzled spectators near a barn that appears as old as Irving’s story. Ghost stories abound, while folk music is played by a campfire.

Adrian Sexton is having a scary good time as a tour guide on the Discovery Walk and a storyteller at the Twilight Village. Her October days and nights have been filled with families looking for some atmospheric fun this time of year.

“A friend of mine in the improv community sent me the job description,” Sexton said in a recent Zoom interview. “She was like, ‘I can’t think of anybody else who could do this but you,’ based on my background in improv comedy, and I’m also a tour guide in the city. With that performative element, it was a natural thing. I must do this. I have to make this happen. Then being able to create something, perfect something and then bringing it to the public, it just adds a whole other element in being able to see the reactions, see what works, play up certain things you didn’t think would get laughs or a reaction, so it’s been a lot of fun.”

Sexton said the Legend of Sleepy Hollow Discovery Walk was designed to capture individuals who head to Sleepy Hollow country looking for some not-so-scary fun times during the Halloween season. She said this walk through the grounds of Philipsburg Manor is a perfect choice to relive the Legend.

“The Discovery Walk is a perfect thing for individuals who are looking for a tie-in to the location with something seasonally appropriate, and also with Twilight, it’s absolutely gorgeous how they’ve done the location,” she said. “It’s family friendly and really sweet. It’s been really nice to see people being dazzled and see them have that experience, from the performer’s side but also as myself. Oh wow, they did a really great job here.”

As a tour guide, Sexton said she appreciates that the programming at Historic Hudson Valley is Halloween-focused but not filled with gore and salaciousness. In many ways, the Discovery Walk and Twilight Village remind her of being a child and finding wonderment this time of year. “It is really nice to see a return to the type of Halloween that I love, which was appropriate for my age, if I was young,” Sexton said. “And also something that parents can enjoy and say, ‘Oh, it was a time well spent.’ They can have the adult beverage, and the kid can have the chocolate. Everybody wins.”

Sexton said performing these parts has been an honor because she can see the reactions of people who are new to the area. She can appreciate how they are expecting some type of Halloween Disney World, but instead they walk away appreciating how Philipsburg Manor is an actual place with a real history.

“There are so many different layers to it; it’s remarkable,” she said. “Surprisingly there have been a lot more adults on the Discovery Walks than I thought at first. I thought it would be more toward kids, but so far, the adults you can see them piecing together what they remember from the story if they saw the Disney cartoon years ago and piecing it with actual real-life events and history. It’s cool.”

When Sexton tells ghost stories in the barn building during the Twilight Village, she pulls from Irving’s text in unique ways. Rather than simply retelling the story everyone knows (the one with that Hessian soldier without a head), she digs deep into the other lore that populates the region, tales of Revolutionary War figures who may still haunt these environs.

“In the story of The Legend of Sleepy Hollow, it’s not just the Headless Horseman that haunts the area,” Sexton said. “There’s Major John André. There’s Mother Hulda. There are pirates burying treasure in the Hudson, and so even though it’s just a sentence, I imagine readers in the 19th century reading it who aren’t from New York, they’re like, ‘Oh, this place is so magical and strange.’ But it actually is rooted in these people’s legends and their lore, and so following up and reading up on those other legends beyond the Headless Horseman has been a really exciting dive. You only hear little snippets here and there, but it’s like, wow, it’s all real.”

In preparation for her autumn of mystery and macabre, she re-read Irving’s story a few times. Every time she dove back into the text, she would find something new to appreciate.

“The first read, you’re reading it as a horror story, but it’s actually really funny,” she said. “Then the second time, you read it for its literary brilliance. There was no Netflix, so he had to throw everything in there to really paint the picture. He’s writing from memory because he wasn’t even living at Sleepy Hollow or in Tarrytown at the time. It’s so beautifully written. … In all the stories, the thing that really stuck out to me are the legends, the stories, the ghosts that haunt the area, it all derives from the American Revolution, and so he’s writing to an audience, if they’re adult, they would have remembered it. It would have been, oh, 40 years ago. … What does this all mean to people who would have remembered all the things that happened during the war?”

By John Soltes / Publisher / John@HollywoodSoapbox.com

The Legend of Sleepy Hollow Discovery Walk and Twilight Village at Sleepy Hollow are both being presented by Historic Hudson Valley through Sunday, Nov. 3, at the Philipsburg Manor in Sleepy Hollow, New York. Click here for more information and tickets.

Adrian Sexton is a tour guide during the day on the Legend of Sleepy Hollow Discovery Walk and storyteller by night at the Twilight Village at Sleepy Hollow. Photo courtesy of the artist / Provided with permission.
The Legend of Sleepy Hollow Discovery Walk, located at Philipsburg Manor in Sleepy Hollow, New York, features a retelling of Washington Irving’s famous tale. Photo by John Soltes.
The Legend of Sleepy Hollow Discovery Walk features a retelling of Washington Irving’s famous tale. Photo by John Soltes.
The Twilight Village at Sleepy Hollow takes over the grounds of Philipsburg Manor for some spirited fun. Photo by John Soltes.
The Twilight Village at Sleepy Hollow takes over the grounds of Philipsburg Manor for some fiery fun. Photo by John Soltes.

John Soltes

John Soltes is an award-winning journalist. His writing has appeared in The New York Times, Earth Island Journal, The Hollywood Reporter, New Jersey Monthly and at Time.com, among other publications. E-mail him at john@hollywoodsoapbox.com

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